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It could very well be, but vaporizing fraction #3 and then #2 the following day both gave the effects of nearly pure bufotenine. Which was a surprise for SWIM. Fraction #1 felt like DMT N-Oxide with no bufotenine effects felt at all.


The following compounds have been found in Anadenanthera (according to several different sources)


XLogP    Compound

?.?    2-methyl-6-methoxy-1,2,3,tetrahydro-beta-carboline

?.?    1,2-dimethyl-6-methoxy-1,2,3,4-tetrahydro-beta-carboline

1.0    Serotonin

1.3    Bufotenine N-oxide

1.4    N-methyl-serotonin (Unknown activity)

1.6    Bufotenine

1.7    2-methyltryptoline (2-methyl-1,2,3,4-tetrahydro-beta-carboline)

1.7    DMT N-oxide

1.7    5-MeO-NMT (Unknown activity)

1.8    N-methyl-tryptamine (NMT) (Unknown activity)

1.9    5-MeO-DMT (Active at 2-10 mg)

2.0    DMT


The XLogP information for two of the three beta carbolines found in Anadenanthera is unknown. So I have no idea where they would be eluted, or if they stayed on the column. But one of them, 2-methyltryptoline, might elute along with bufotenine. It has a similar XLogP, but is slightly less polar.


SWIM’s tests show that pure ethyl acetate could not elute bufotenine, but did elute a DMT N-Oxide like compound that crystallized. So it’s likely that pure ethyl acetate could only elute everything from XLogP 1.7 and up. That would include the beta-carboline 2-methyltryptoline.


SWIM’s tests show that ethyl acetate with 25% methanol is able to elute nearly pure bufotenine (after eluting with pure ethyl acetate) along with a brown or amber material that might be some 2-methyltryptoline coming through. Whatever the amber stuff is, it seems to have little activity in the 7 mg dosage range tested. So it would appear that ethyl acetate with 25% methanol is able to elute everything from XLogP 1.6 and up. If the amber or brown material is one or more of the beta carbolines above, then they are very weak compared to bufotenine.


According to other papers, serotonin elutes with dilute hydrochloric acid. So it should not elute with methanol, or if it does it should take tons of solvent to elute it.


N-methyl-serotonin is fluorescent. I can’t find much information about it. It’s much less polar than serotonin and bufotenine N-Oxide. It’s possible that it is eluted with ethyl acetate with 75% methanol.


The main reason for this work is to find out what’s causing the side effects, and to remove them. From this test it’s clear that the side effects are caused by compounds that are more polar than bufotenine and can therefore be easily removed. But which one of the more polar compounds are responsible for the side effects? Serotonin? Bufotenine N-oxide? N-methyl-serotonin? Or one or more of the beta-carbolines? Or a mix of them?


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